Diisopropylethylamine → HCID 11500190, compound

HRID 2358314Notes

Reaction equation

HRID 2358314 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][NH2:10].C(N(C(C)C)CC)(C)C.[C:20]1([CH:26]([CH2:30][CH3:31])[C:27](Cl)=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][NH:10][C:27](=[O:28])[CH:26]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 981732-Phenylbutyryl chlorideHCID 177507992-Fluoro-5-methylbenzenemethanamine

Product 1

HCID 11500190HCID 11500190, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2-fluoro-5-methylphenyl)methanamine (1-f, 50 mg, 0.26 mmol, Oakwood Products, Inc., West Columbia, S.C.) and diisopropylethylamine (88 uL, 0.52 mmol) in dichloromethane (1 mL) was treated at room temperature with 2-phenylbutanoyl chloride (1-a, 47 mg, 0.26 mmol). The reaction mixture was stirred for 30 min, partitioned between dichloromethane and 0.1N—NaOH. The aqueous layer was removed and the organic layer washed with 0.1N-HCl. The aqueous layer was removed by filtering through a plastic frit. The organic layer was evaporated in vacuo to give the desired product (1-2); HRMS (M+1)=286.1586.

Workup

  1. custompartitioned between dichloromethane and 0.1N—NaOH
  2. customThe aqueous layer was removed
  3. washthe organic layer washed with 0.1N-HCl
  4. customThe aqueous layer was removed
  5. filtrationby filtering through a plastic frit
  6. customThe organic layer was evaporated in vacuo

Sources & evidence

ORD record
ord-97921262ea7e4e709a1d794aa21b86bc
Source dataset
uspto-grants-2010_07
Patent number
US07763659B2

Reaction notes

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